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MTV's notorious stunt-and-prank show, in which a crew of grown men hurt themselves for your entertainment. Premiering on October 1, 2000, it strung together shopping-cart crashes, ill-advised dares, and gross-out gags performed by Johnny Knoxville, Bam Margera, Steve-O, and the rest of the gang. Wrapped in stern on-screen warnings not to try any of it at home, it was appointment viewing for a generation of teenagers — and the launchpad for a movie franchise that's still going.
Miniature fingerboards the size of trading cards that let you do tricks on your desk. Tech Deck's genius move was licensing graphics from real skate brands like Birdhouse and World Industries, turning a novelty into a collecting frenzy — and a classroom contraband item teachers confiscated by the drawerful.
Activision and Neversoft's skateboarding game, first released in 1999, about chaining tricks into massive combos and collecting the letters S-K-A-T-E across increasingly iconic venues. The punk, ska, and hip-hop soundtrack defined the era. Tony Hawk's Pro Skater 2 (2000) is widely considered the series' peak and one of the best games ever made.